A mild synthetic route to α-nitroso diaryl pyrroles (Postprint)
Date
2024Author
Brown, Emily B.
Gapare, Rosinah Liandrah
Campbell, Jacob W.
Alkaş, Adil
Sequeira, Steve
Hilborn, James W.
Greening, Sarah M.
Robertson, Katherine N.
Thompson, Alison
Metadata
Show full item recordAbstract
A new synthetic method to access α-nitroso pyrroles is presented. This method utilises the nitrosonium salt NOBF4, enabling short reaction times (<10 minutes) and avoiding the harsh acidic conditions usually associated with pyrrole nitrosation. Application of this procedure to diarylated pyrroles yielded several novel nitroso-pyrroles. Modifications to the method, through exclusion of air and inclusion of a mild base, allowed for the nitrosation of pyrroles bearing aryl groups substituted with electron-donating groups. Attempts to nitrosylate pyrroles bearing alkyl substituents resulted in the formation of a dimeric material composed of a pyrrolic unit and a 2-hydroxyimino-protected 1,5-dihydro-2H-pyrrol-2-one.
Citation
Published Version: Brown, E. B., Gapare, R. L., Campbell, J. W., Alkaş, A., Sequeira, S., Hilborn, J. W., ... & Thompson, A. (2024). A mild synthetic route to α-nitroso diaryl pyrroles. Organic & Biomolecular Chemistry, 22(30), 6122-6128.